


Spelunkers

by mattzerella_sticks



Series: Season 14 Inspired [6]
Category: Supernatural
Genre: Awkward Dean Winchester, Bisexual Dean Winchester, Bottom Dean Winchester, Cave diving, Cowboy fantasies, Dean letting himself enjoy things without feeling shame, Dean's past, Fingering, John Winchester's A+ Parenting, M/M, Masturbation, Post 14x04, Spelunking, clueless Sam Winchester, dildos and vibrators, toxic masculinity
Language: English
Status: Completed
Published: 2018-11-02
Updated: 2018-11-02
Packaged: 2019-08-16 18:47:35
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,429
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16500770
Author URL: https://archiveofourown.org/users/mattzerella_sticks/pseuds/mattzerella_sticks
Summary: Post 14x04Dean's riding the high of his adventure in Salem, and decides to invest in something he's always wanted, but was too shameful to buy. However, now that he did, the fear resurfaced, and he's not sure if it was a good idea. Will Dean decide to experience the pleasure, or let the pain overwhelm him before he even begins.





	Spelunkers

**Author's Note:**

> So I'm not done obsessing over 14x04! Especially after reading the meta-analysis talking about Dean killing the toxic shadow of John and deciding to drop his 'performance' of masculinity and letting himself enjoy things he wasn't allowed to when he was younger!
> 
> That being said enjoy this sexy one-shot ; )

            Dean knows he shouldn’t feel so scared. The cardboard box isn’t cursed or haunted. But still, it sits on his lap – menacingly. As if taunting him every time his fingers inch closer towards the opening flaps. It’s surprising he’s even _looking_ at it given his eyes were too focused on… _anything_ _else_ when he snatched the box from the shelf.

            ‘ _It’s normal_ ,’ he tells himself once more, ‘ _No one thinks you’re weird because you bought it_.’

            Except the girl behind the counter definitely judged him during checkout, raising a wry brow and scanning him before the item. He barked out a rough “What?” hoping his face wasn’t too red. She had just shrugged and mumbled out a sarcastic “ _Nothing_.” Dean tossed the money on the counter before she could finish bagging, not even bothering with change. It’d have been easier to pay with card, but the girl at the store was already one-person too many than he was comfortable knowing about his purchase. Cards leave a trace – and _anyone_ could look through that.

            ‘ _Although I shouldn’t be uncomfortable_ ,’ he thought, ‘ _People buy this kind of stuff all the time._ ’

            But Dean Winchester isn’t just any people. He’s _never_ bought a dildo before – until _today_.

            Dean psyches himself up. “You can do this. It’s nothing you haven’t seen before… Just think of it like an angel blade – except _softer_ and more latex-y… _Christ_.” He drags his hands down his face, peeking between the fingers at the box. “It’s just a fake penis, what’s the problem?”

            He knows what the problem is. It’s that he’s never felt so unguarded and _safe_ before. Here, in his room, surrounded by his favorite books, his collector’s guns, dirty laundry and empty cans, there’s no one around to watch him _enjoy_ something Dean thought was fun.

            Dean tried before, but there was always at least one set of eyes that held him at bay. Like John, who caught Dean having too much fun with Baby’s engine by sitting on her hood. Or Sam, who could always spot whatever Dean tried to hide in their motel room-of-the-week. Even girls he’d hook up with would laugh and grab their toys from him when he toed the line of friendly curiosity.

            ‘ _Who cares what others think anyway? You’ve been through too much to **not** enjoy the things you like_.’

            He makes a fair point to himself. Over the years, Dean has toned down his guard and stopped policing his actions. Their last case was a testament to how free he’s felt, exchanging e-mail addresses with Dirk so they could stay in touch and ‘talk shop’. Barely-legal Dean would have given Stuart the brush-off before verbally tearing him a new asshole for liking comics. But then again, maybe only after John had prodded him with a “Get a load of this, freak.”

            ‘ _And it’s not like you’ve done more embarrassing stuff in other places.’_

Dean blanches at his subconscious reasoning, images of grimy showers, complimentary soap on slender, shaking fingers, being two knuckles deep as he yelled over the crappy water pressure “I’ll be done in a few minutes, Sam, don’t bust the door down!”

            ‘ _That’s not the same though_ ,’ he plays devil’s advocate now, ‘ _those weren’t **meant** to be jammed in there – just an added bonus. This… there’s nothing else you can do with a dildo **but that**.’_

            And Dean’s not sure he’s ready to own a dildo. Ownership defines you. Dean’s not sure he wants that definition to encompass him as if the roles of him and his purchase were reversed. If he removes it from the box now, there’s no way he could chicken out and return it.

            But then he also won’t get to experience all the _pleasure_.

            “On the count of three,” he says, rapping his fingers on the box, “One… two… _three_!” He pries it open and dumps it onto his bed. Now, out of the box, Dean gets a good look at it. The dildo’s purple in color, with a handle at the end of the shaft the looks like a small ball-sack. ‘ _Or maybe it’s normal size_ ,’ he thinks, picking it up, ‘ _since this is **longer** than I thought…’_ Dean feels the toy out, kneading at the latex, pinching the head to test the firmness. When he gets towards the other end, his fingers press into a button, and it comes to life.

            “ _Shit!_ ” he yelps, dropping the writhing dildo back onto his bed. It wiggles, mussing up his sheets, and causing Dean’s face to discover a new shade of red.

            “Crap,” he mutters, “I picked up a _vibrator_.”

            Which makes the situation even more _frightening_. All Dean had wanted to do was test the waters, not cannonball into them. But here he is, fully submerged and with a vibrator dancing inches away.

            Dean widens that distance. He stands and starts to pace the length of his room, every now and then glancing at it. In between his worry, Dean checks and re-checks the locks on his door. Seeing as the situation has already fumbled down from bad to worse, Dean wants to make sure it doesn’t completely descend into _worst_ by having someone walk in on him and his new dancing friend.

            He’s already had enough close calls during the build-up to this.

            The most memorable a few nights ago, in the kitchen, Dean surfed the web for more information on the different kinds of pleasure toys that were out there and how to use them. It was late in the night, and even with the Bunker transitioning into a veritable Hunter’s Motel, he still felt like the room afforded some privacy. Especially since no one really knew him well enough to ask what he was looking at.

            Unless Sam decided to walk in – which, of course, he did.

            “Hey, Dean, what’cha doing?”

            He slammed the laptop lid too fast for it to be anything _but_ suspicious. Sam’s ‘worried brother’ mask slipped back on, and he tilted his head the way he would if talking to a wounded animal – something Dean’s become more familiar with in recent weeks.

            Dean still tried to throw him off. “What?”

            “What were you looking at on your laptop?” Sam continued, nodding towards the device. Dean blinks at it before turning back to Sam, a somewhat blank look on his face.

            “…Case.”

            “A case?” Sam parroted, “Really?”

            “Don’t believe me?”

            “I mean, why wouldn’t I,” Sam said, hands splayed up and out, deferring the accusation. He switched paths towards the fridge and grabbed two beers, bringing them over to the table and taking the seat opposite Dean. He slid the other bottle over before opening his own. The laptop sat at an equal distance between both of them. “Besides,” he shrugged, “Not like you’d do anything _stupid_ like look up porn now that we have _guests_.”

            Dean’s lip twitched. “Naturally.”

            “So,” Sam gestured to it, “Why don’t you show me?”

            “Um – what?”

            “The case,” he wiggled his eyebrows, “Y’know… the thing you were looking up?” His eyes gave him away, delighting too much in his brother’s uncomfortableness. Dean has the thought to show him, watch the humor wither and die off his face at his search history, but decided against it. He wouldn’t enjoy Sam’s horror given he’d be dead from embarrassment before the first light of Sam’s innocence faded.

            Still, he needed to say something.

            “Alright,” he sighed, “You got me.”

            “I knew it, Dean –“

            “I wanted to surprise you, but apparently I’m horrible at keeping things from you.” He fiddled with the label of the drink, hoping Sam takes the bait. Like a dog with a bone, Sam snatched up the breadcrumbs Dean dropped.

            “A surprise?”

            Dean nodded. “Yeah, I figured you and I should do something, together – non-case related. I had fun in Salem but it was, uh… a bit of the same?” He chuckled, “I mean how many times can you fight ghosts with your brother before it becomes old hat?”

            “I see what you mean.” Sam’s eyes darted back to the laptop, hands twisting around the neck of the bottle. “So… what were you –“

            Dean swiped his computer back before Sam could even think his question. “I thought we could –“ ‘ _Think, Dean, think. Not the truth, but something close – so it’s not hard to –‘_ “go spelunking.”

            “…Spelunking?”

            “Yep!” Dean grimaced, mentally stabbing the part of his brain that came up with the lie. “Y’know, _cave diving_? I thought it could be fun. I mean, _I’ve_ always been a fan of it –“

            “Really?” Sam asked, tone dripping in disbelief, “You? Enjoying something outdoors?”

            Dean grit his teeth. “Even I surprise myself sometimes.” Clearing his throat, he tried to turn the tables and make Sam feel bad. “Although I’m not sure you’d enjoy it, really. Takes a true man to appreciate the beauty of – ah… _caves_. Understand the work and effort needed to _explore_ … I could call Cas, I’m sure he’d _love_ to explore my ca… explore caves with _me_. Or I could go it alone? I’m used to it these days since you’re so busy running shop here…”

            He sagged in relief when he noticed how Sam’s face shifts into his ‘maybe-I’m-being-a-horrible-brother’ expression.

            “You really want to go spelunking?”

            He sealed the deal with some truth. “It’s something I’ve always wanted to try, but never thought I _could_.” That’s how he escaped the situation, with Sam’s muttered ‘I’ll think about it’ and a second beer. Dean ran back to his room the minute he could.

            Although now, with the battery-powered worm on his bed, it’s not as safe as he once thought.

            “It’s just a vibrator,” Dean tells himself, wringing his hands clumsily, “And what’s a vibrator, really, but a dildo without training wheels, hmm?” Even to him his laughter sounds false. “Okay, you can make this work just – just turn it off.”

            The first attempt is sad. He reaches for it only to jump back after it ‘launches’ itself at him. But with a few more words of encouragement and readying slaps to the face, Dean musters the strength to grab the writhing toy and turn it off.

            Only now, vibrator in hand, he has no idea what to do next.

            ‘ _I mean there’s only two choices now_ ,’ he thinks, ‘ _I could hide this under my bed, wait until everyone’s asleep, and burn this out in the woods, or…_ ’

            He sits back on the bed, opting for the latter. Dean reaches for his ‘special’ drawer, digging past tissues, old issues of Busty Asian Beauties, printouts of his favorite actors, and candid pictures of Cas before he finds the lube. Dumping it on the nightstand, he then unbuttons his pants and shimmies out of his clothes. He looks to his left and laughs at the sight. In his faded, brown Henley, and nothing else, he looks like a sad version of Winnie the Pooh.

            “Okay, let’s not make _that_ the thought we start this with _,_ ” he says, pumping out two squirts of lube. Dean coats his fingers liberally, adding an extra squirt for safety. He gets into position, on his back, and uses his non-lubed hand to hitch his leg up and out of the way.

            His body knows this time it’s different. Unlike the other nights where his hole wastes no time in accepting his fingers, already used to the feel of them, his body stays tight and puckered, aware that Dean’s hand is just the appetizer. Slipping the first one in is a feat of itself, the walls clenched tight around it. Dean hisses in a sharp breath as he knocks against it, hoping he can wiggle enough space to slip the next one in.

            After a few minutes of labored pumping, Dean thinks he’s ready to push the second finger in. It’s a tight squeeze (‘ _Feels like I’m twenty all over again_ ’) but he squeezes it in there.

            Now with both fingers deep inside himself, Dean gets to work. He pushes in and out, scissoring with every other thrust. The third time hits a familiar bundle of nerves and causes his dick to _thwump_ against him. ‘ _Jackpot_ …’ He rocks into his hand now, using his wrist and ass to start a sweet rhythm, his heavy boner bouncing with the motions. Dean starts having _too_ much fun then, even popping his hand out to squirt some more lube to add a _third_ finger. “Oh yeah,” he grunts, curving the fingers just right, “so so so so nice…” It’s intoxicating. Dean even rubs his leaking dick for a few minutes, teasing it, letting it build and build but pulling away just as he hits the edge.

            In the whirlwind of his pleasure, he notices the discarded vibrator off to the side – close enough to his ass without actually being inside it. ‘ _Remember why you started pleasuring yourself?_ ’ he thinks, movements slowing, ‘ _It’d be a waste if you didn’t use it now._ ’

            “Alright,” he says, “C’mere.” He pulls his fingers out and grabs the toy. Still feeling cautious, he slathers it in lube, practically jerking the toy off in his hand. “Okay… it shouldn’t be so bad. Remember, you’re already loose… should slip in nice and easy.”

            It barely moves. Not that his hole has tightened up; instead, Dean holds it right up to the entrance, but can’t move it further. Instead he stares at it, afraid that if he looks away it might start up again.

            “This is ridiculous,” he sighs, pulling the vibrator away, “I’m not letting a stupid piece of plastic get the better of me!”

            Dean decides to try a different tactic. He shifts, dragging his pillow to the foot of the bed and collapsing on it, chest first. Then, he raises his ass in the air, positioning the vibrator just so, with his hands around the middle. Closing his eyes, Dean pushes in. It’s a tough fit, and Dean has to use his other hand to open his hole enough for the silicon to slip through.

            ‘ _This… ain’t so bad_?’

            Dean wiggles his ass, adjusting to the girth of his toy. He even adds an extra couple of inches inside, bringing the hilt closer to his body. The size is something he isn’t used to, but the pleasure makes up for the pain. Resuming his ministrations, he picks up his pace and slides the toy in and out, his ass rocking with it on the off-beat. Dean’s hole tightens from time to time, forcing a ragged moan from his lips. A few times he has to bite down on the pillow so he doesn’t scream.

            “That – that feels so nice, Gunner…” he fantasizes about his hero, deciding his first try with his toy should be with the same person he fantasized about when fingers would lightly graze his ass during the shower. Except the old dream does nothing for him, sounding off to his own ears. “Alright,” he tries again, eyes closed, “Doc Holliday? Maybe helpin’ Wyatt Earp with his aim?” His dick twitches with interest slightly, but not with the same surge from before. ‘ _Close_ ,’ he thinks, ‘ _But not perfect. Why can’t I think of_ –‘

            In his distraction, he doesn’t realize his hand slipping on the base. He tries to regain hold, but the force he used reclaiming his grip had another side effect. The vibrator turns on once more, now fully sheathed inside Dean, and presses a decent amount of pressure onto Dean’s prostate.

            “All that’s sweet and holy,” Dean cries, eyes flying open, “ _Caaaass!_ ” His body crackles with energy, as if he’d become one, giant frayed nerve. The sheets, his shirt – it all rubs at him and sets off a chain reaction that boils down to pleasure, pleasure, and more pleasure.

            Dean keeps pumping, practically humping his bed given the motion of his hips. His dick rubs up and down his sheets, his hands too busy to do anything to help. While one wrestles with the vibrator in his ass, the other claws into his pillow. Dean acts on autopilot, moving faster and faster. The images in his mind supplying the scenario – where a certain-blue eyed angel leaves his mark on his hips. Thrusting into Dean, calling him ‘ _babe_ ’, ‘ _sweetheart_ ’, ‘ _mine_ ’, and ‘ _huckleberry_ ’. The Cas in his head treats Dean like a bucking bronco or a mechanical bull, and the thought of his angel whipping his cowboy hat in a lazy arc hurdles him over the final barrier.

            Dean comes all over himself and the bed, leaving a huge wet spot. He tries to pick himself up, but he’s too exhausted – preferring to stick to the bed rather than clean up. However, Dean does muster the energy to pull the vibrator out of his ass. The way it wriggled around, it might have prepped him for a second round he wasn’t ready for.

            He tosses it, letting it land in a pile of discarded plaid and muddy jeans.

            “That was… _awesome_.”

            The bliss doesn’t last too long. Someone knocks on his door, startling him from the heavy sleep that started to descend. “Dean?” Sam calls from the other side, “Is everything okay in there? I thought I heard something?”

            ‘ _Crap crap crap crap crap!_ ’

            He panics. Everything goes wrong. In his haste to stand, Dean didn’t realize how jelly his legs were, and he crumples in on himself, slamming into his already sore ass. He bites down a curse, shedding a single tear before pulling himself up once more. He winces into his jeans, using his underwear to wipe at the mess on his chest and then tossing it onto the pile. That’s followed by his sheets, which he bundles up and dumps on top of the laundry pile. Dean grabs the vibrator and the lube and throws it into his special drawer. Surveying the room one final time, he moves to open the door for Sam.

            He feigns innocence. “Yes?”

            Sam looks past him at the room, scanning for something _amiss_. “I wanted to know if you were all right?”

            “All right?” Dean scoffs, “Why wouldn’t I be all right?”

            “I don’t know,” Sam says, pouting, “Maybe because I heard shouting in here a few minutes ago?” He glances at the bed. “Did you have a nightmare or something?”

            “No.”

            “Then why are the sheets –“

            “Jesus, Sammy, _you_ were the one who used to piss the bed, not me,” Dean shifts focus, “Y’know adults do this thing called ‘washing the sheets’? Maybe if you weren’t too busy researching and did some chores you’d understand.” The flat look Sam shoots him is a welcome change.

            “Okay, whatever,” he sighs, looking at Dean, “I needed to tell you something anyway.”

            “Go ahead.”

            “I’ve been talking it over with a few of the people here, especially Mom and Bobby, and they said it’d be fine if we took a few days off.”

            “…What?”

            “For our spelunking trip?”

            Dean’s stomach drops. He’s surprised it isn’t here now, rolling on the floor, given how loose and slippery his asshole is. “Our trip?” he asks, faking enthusiasm, “Yay…”

            Sam carries on. “Anyway I know _you_ were planning it, but I did some research as well – and get this. There’s a series of caves near Kansas City as well as some mineshafts I thought looked cool. On this website, a lot of people who do this stuff as a hobby and they only recommended it, said it’d be a great tour. It’s even got a place where we can rent all the stuff we need! So I was thinking we head out tomorrow and do as many as we can for three or four days… sound good?”

            “Totally… awesome.”

            “Great!” Sam smiles, patting Dean on the shoulder. He wants to say something more, but his nose twitches, and his grin falls. “Dean, are you sure –“

            “Okay, gotta get packing – bye!”

            He slams the door closed, locking it for good measure. Dean spins on his heel, walking back towards his special drawer. Pulling out the dildo, he wrinkles his face at the mess. It’s still a tad slimy – but thankfully only a magazine and a half-faded picture of Harrison Ford suffered the most in his haste. He tosses those in his trash can before wiping down his toy with a discarded shirt.

            “You know, for such a small vessel,” he says, “you sure do pack a lot of power…” The reminder of his potent orgasm sends shivers down his spine. Dean thinks back to his fantasy. “Hopefully the real thing is even better.”

            He nestles his vibrator back into the drawer and closes it with a smile.

            ‘ _So_ _worth it._ ’

**Author's Note:**

> Did ya like? I gotta say that I had a lot of fun writing this, and who knows? With how much they love referencing to things off-screen in subtext, maybe this did happen after?


End file.
